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A kind of compound 3-methyl-4,5-dichlorothiophene-2-carboxylic acid and its preparation method

A technology of dichlorothiophene and methylthiophene, which is applied in the direction of organic chemistry, can solve the problems of harshness, old methods, and high risk, and achieve the effect of promoting production, short synthesis route, and easy processing and purification

Inactive Publication Date: 2020-02-18
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of chlorothiophene compounds reported in the literature is mostly realized under harsh chlorine gas conditions, which is dangerous, highly toxic, difficult to operate and pollutes the environment, which greatly limits the efficient preparation and application of halogenated thiophene compounds. need
At present, there are very few reports on the synthesis method of dichlorothiophene. For the compound disclosed in the present invention: 3-methyl-4,5-dichlorothiophene-2-carboxylic acid, the literature that can be retrieved is reported in 1938, Not only the method is old and harsh, but also the use of chlorine gas for chlorination has a very large operational risk and environmental pollution. So far, no new literature reports have been seen.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The synthetic method of present embodiment 3-methyl-4,5-dichlorothiophene-2-carboxylic acid is as follows:

[0017] Take a 50ml single-necked bottle, add 2.84g (0.02mol) of 3-methylthiophene-2-carboxylic acid, and add 30ml of a mixed solvent of acetic acid and N,N-dimethylformamide with a molar ratio of 1.0:1.0, and stir After dissolving, 10.65 g (0.08 mol) of N-chlorosuccinimide was added. After stirring evenly, heat it with a hair dryer to initiate the reaction, put it in an ice bath, take it out after cooling down, and stir at 35°C for 6 hours. Afterwards, the reaction solution was poured into a separatory funnel, and an appropriate amount of water and ethyl acetate were added thereto for extraction twice. Wash the ethyl acetate layer with water 3-4 times, combine the water layers, extract once with ethyl acetate, then wash the ethyl acetate layer twice with water, combine the organic layers, remove the solvent with a rotary evaporator, and use a column layer for th...

Embodiment 2

[0023] The synthetic method of present embodiment 3-methyl-4,5-dichlorothiophene-2-carboxylic acid is as follows:

[0024] Take a 50ml single-necked bottle, add 2.84g (0.02mol) of 3-methylthiophene-2-carboxylic acid, and add 30ml of a mixed solvent of acetic acid and N,N-dimethylformamide with a molar ratio of 1.0:1.5, and stir After dissolving, 10.65 g (0.08 mol) of N-chlorosuccinimide was added. After stirring evenly, heat it with a hair dryer to initiate the reaction, put it in an ice bath, take it out after cooling down, and stir at 35°C for 6 hours. Afterwards, the reaction solution was poured into a separatory funnel, and an appropriate amount of water and ethyl acetate were added thereto for extraction twice. Wash the ethyl acetate layer with water 3-4 times, combine the water layers, extract once with ethyl acetate, then wash the ethyl acetate layer twice with water, combine the organic layers, remove the solvent with a rotary evaporator, and use a column layer for th...

Embodiment 3

[0026] The synthetic method of present embodiment 3-methyl-4,5-dichlorothiophene-2-carboxylic acid is as follows:

[0027] Take a 50ml single-necked bottle, add 2.84g (0.02mol) of 3-methylthiophene-2-carboxylic acid, and add 30ml of a mixed solvent of acetic acid and N,N-dimethylformamide with a molar ratio of 1.0:2.0, and stir After dissolving, 10.65 g (0.08 mol) of N-chlorosuccinimide was added. After stirring evenly, heat it with a hair dryer to initiate the reaction, put it in an ice bath, take it out after cooling down, and stir at 35°C for 6 hours. Afterwards, the reaction solution was poured into a separatory funnel, and an appropriate amount of water and ethyl acetate were added thereto for extraction twice. Wash the ethyl acetate layer with water 3-4 times, combine the water layers, extract once with ethyl acetate, then wash the ethyl acetate layer twice with water, combine the organic layers, remove the solvent with a rotary evaporator, and use a column layer for th...

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Abstract

The invention discloses a novel compound 3-methyl-4,5-dichlorothiophene-2-carboxylic acid with the following structural formula defined in the specification. A preparation method of the compound 3-methyl-4,5-dichlorothiophene-2-carboxylic acid comprises the following steps: adding 3-methylthiophene-2-carboxylic acid into an acetic acid and N,N-dimethylformamide mixed solution, adding N-chlorosuccinimide in ice bath, and carrying out a reaction at the temperature of 25-35 DEG C for 4-6 h to obtain 3-methyl-4,5-dichlorothiophene-2-carboxylic acid. The synthetic route disclosed by the invention is short and only comprises one step, the used preparation method is simple to operate, the reaction is relatively mild, the product is easily treated and purified, and the preparation method is a method suitable for batch preparation. As such the compound is a valuable functional intermediate, the compound disclosed by the invention has important research and practical value, and the preparation and production of other similar derivatives can be greatly promoted.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, and in particular relates to a novel compound 3-methyl-4,5-dichlorothiophene-2-carboxylic acid and a preparation method thereof. Background technique [0002] Thiophene compounds are not only good fragments of optoelectronic materials, but also have various pharmacological activities. In recent years, studies have found that compounds containing thiophene structures have good therapeutic effects. anti-inflammatory effect with low toxicity. However, the synthesis of chlorothiophene compounds reported in the literature is mostly realized under harsh chlorine gas conditions, which is dangerous, highly toxic, difficult to operate and pollutes the environment, which greatly limits the efficient preparation and application of halogenated thiophene compounds. need. At present, there are very few reports on the synthesis method of dichlorothiophene. For the compound disclosed in the present i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/38
CPCC07D333/38
Inventor 靳清贤王明花徐粉胡路平甄摇摇秦旭东
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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